Dolasetron

Title: Dolasetron
CAS Registry Number: 115956-12-2
CAS Name: 1H-Indole-3-carboxylic acid (2a,6a,8a,9ab)-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester
Additional Names: endo-hexahydro-8-(3-indolylcarbonyloxy)-2,6-methano-2H-quinolizin-3(4H)-one
Manufacturers' Codes: MDL-73147
Molecular Formula: C19H20N2O3
Molecular Weight: 324.37
Percent Composition: C 70.35%, H 6.21%, N 8.64%, O 14.80%
Literature References: Bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Prepn: M. W. Gittos, EP 266730; idem et al., US 4906755 (1988, 1990 both to Merrell Dow). Binding study: P. H. Boeijinga et al., Eur. J. Pharmacol. 219, 9 (1992). Pharmacology: R. C. Miller et al., Drug Dev. Res. 28, 87 (1993). Clinical pharmacokinetics: H. Boxenbaum et al., Biopharm. Drug Dispos. 13, 693 (1992); eidem, ibid. 14, 131 (1993). GC-MS and LC determn in plasma: T. A. Gillespie et al., J. Pharm. Biomed. Anal. 11, 955 (1993). Clinical trial in emetogenic chemotherapy: A. A. Fauser et al., Eur. J. Cancer 32A, 1523 (1996); for prevention of postoperative nausea: S. G. Graczyk et al., Anesth. Analg. 84, 325 (1997).
Derivative Type: Methanesulfonate
CAS Registry Number: 115956-13-3
Additional Names: Dolasetron mesylate
Manufacturers' Codes: MDL-73147EF
Trademarks: Anzemet (Aventis)
Molecular Formula: C19H20N2O3.CH3SO3H
Molecular Weight: 420.48
Percent Composition: C 57.13%, H 5.75%, N 6.66%, O 22.83%, S 7.63%
Properties: Crystalline solid, mp 278°.
Melting point: mp 278°
Therap-Cat: Antiemetic.
Keywords: Antiemetic; Antimigraine; Serotonin Receptor Antagonist.
DOM Domesticine Domiodol Domiphen Bromide Domitroban

Dolasetron
Dolasetron.svg
Dolasetron 3D.png
Systematic (IUPAC) name
(3R)-10-oxo-8-azatricyclo[5.3.1.03,8]undec-5-yl 1H-indole-3-carboxylate
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a601001
Pregnancy cat. B (US)
Legal status Rx only
Routes Intravenous, oral
Pharmacokinetic data
Protein binding 69 to 77%
Half-life 8.1 hours
Identifiers
CAS number 115956-12-2 YesY
ATC code A04AA04
PubChem CID 60654
DrugBank DB00757
ChemSpider 16736416 YesY
UNII 82WI2L7Q6E YesY
KEGG D07867 YesY
ChEMBL CHEMBL1201240 N
Chemical data
Formula C19H20N2O3 
Mol. mass 324.374 g/mol
 N (what is this?)  (verify)

Dolasetron (trade name Anzemet) is a serotonin 5-HT3 receptor antagonist used to treat nausea and vomiting following chemotherapy. Its main effect is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata. It does not have much antiemetic effect when symptoms are due to motion sickness. This drug does not have any effect on dopamine receptors or muscarinic receptors.

Dolasetron breaks down slowly, staying in the body for a long time. One dose usually lasts 4 to 9 hours and is usually administered once or twice daily. This drug is removed from the body by the liver and kidneys.